Shibuya is certainly host to many interesting characters, and the longer I am here, the more I see this guy. Standing in centergai with his little bag of pictures, he is somewhat reminiscent of a "catch" guy, but packaged differently and always targeting high school girls. While I think the guy that said he is probably scouting girls for pictures is probably right, I still can't work him out..
Text addendum: turns out that the dude is somewhat of a social worker. His name is Jimmy, and he's even just started his own clothing line.. Thanks to Don for the info!